Sodium Carbonate → N-[2-(6-Chloro-2-pyrazinyl)-4-methylphenyl]-2,2-dimethylpropanamide

HRID 1780587Notes

Reaction equation

HRID 1780587 reaction equation
B([C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:5]=1[NH:11][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])(O)O.[Cl:18][C:19]1[CH:24]=[N:23][CH:22]=[C:21](Cl)[N:20]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.[Cl-].[Na+].O>[Cl:18][C:19]1[N:20]=[C:21]([C:4]2[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:5]=2[NH:11][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])[CH:22]=[N:23][CH:24]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 785042,6-DichloropyrazineHCID 19045057N-(2-borono-4-methylphenyl)-2,2-dimethylpropanamide

Product 1

HCID 19047050N-[2-(6-Chloro-2-pyrazinyl)-4-methylphenyl]-2,2-dimethylpropanamide

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirred mixture of the title compound from Example 1 (3.9 g, 0.017 mol), 2,6-dichloropyrazine (10.0 g, 0.067 mol) and tetrakis(triphenylphospine)-palladium(0) (0.05 g) in glyme (ethylene glycol dimethyl ether, 150 mL) was added aqueous 1M sodium carbonate (67 mL), 0.067 mol). The mixture was heated to reflux and for 8 h. After cooling to room temperature, the mixture was poured into brine (300 mL). The layers were separated and the aqueous phase extracted with three 150 mL-portions of ethyl acetate. The combined organic layers were dried (MgSO4) and evaporated. The residue was chromatographed on silica gel eluting with 20% ethyl acetate/hexane to furnish 4.0 g (78% of theory) of the title compound as a white solid melting at 80°-83° C. 1H NMR (300 MHz, CDCl3) δ 10.75 (br s, 1H), 8.91 (s, 1H), 8.51-8.56 (m, 1H), 8.39-8.41 (m,1H), 7.46 (s, 1H), 7.29-7.33 (m, 1H), 2.40 (s, 3H), 1.32 (s, 9H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux and for 8 h
  3. customThe layers were separated
  4. extractionthe aqueous phase extracted with three 150 mL-portions of ethyl acetate
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. customevaporated
  7. customThe residue was chromatographed on silica gel eluting with 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-00c3c97135d540658c218891f49f9240
Source dataset
uspto-grants-1997_05
Patent number
US05631206

Reaction notes

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